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Winter Park Homes For Sale & Real Estate - 171 homes

Winter Park homes for sale are located in Orange County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

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  • 2107 STAUNTON AVENUE, WINTER PARK, FL 32789

    $324,9002 Days on yellowkey   MLS ID: O5973109

    For Sale O5973109 - 2107 STAUNTON AVENUE, WINTER PARK, FL 32789 0 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1337
       Built: 1942   Tax: $836 (2020)
    Community: Orange Terrace
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,850 (change assumption)
    Mortgage ($1,780) + Taxes in 2020 ($70)

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    Taxes:$836

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 1726 PALMER AVENUE, WINTER PARK, FL 32789

    $989,0002 Days on yellowkey   MLS ID: O5971911

    For Sale O5971911 - 1726 PALMER AVENUE, WINTER PARK, FL 32789 0 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 3199
       Built: 2005   Tax: $11,818 (2021)
    Community: Jenkins Add
    Pool: No

    Single Family


    Estimated Monthly Payment: $6,404 (change assumption)
    Mortgage ($5,419) + Taxes in 2021 ($985)

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    Taxes:$11,818

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2021

    Middle School: Maitland Middle


  • 629 PENN PLACE, WINTER PARK, FL 32789

    $1,250,00020 Days on yellowkey   MLS ID: O5968166

    REDUCED by $49,000 (3.8%) on 09/14/2021

    For Sale O5968166 - 629 PENN PLACE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 3340
       Built: 2000
    Monthly Fee: $159
       Tax: $9,519 (2020)
    Community: Pennsylvania Place Rep
    Pool: No

    Single Family


    Estimated Monthly Payment: $7,801 (change assumption)
    Mortgage ($6,849) + Fees ($159) + Taxes in 2020 ($793)

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    Taxes:$9,519

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 628 PENN PLACE, WINTER PARK, FL 32789

    $1,250,0002 Days on yellowkey   MLS ID: O5973018

    For Sale O5973018 - 628 PENN PLACE, WINTER PARK, FL 32789 0 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3356
       Built: 2001
    Monthly Fee: $159
       Tax: $10,247 (2020)
    Community: Pennsylvania Place Rep
    Pool: No

    Single Family


    Estimated Monthly Payment: $7,862 (change assumption)
    Mortgage ($6,849) + Fees ($159) + Taxes in 2020 ($854)

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    Taxes:$10,247

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 408 WORTHINGTON DRIVE, WINTER PARK, FL 32789

    $799,0002 Days on yellowkey   MLS ID: O5972729

    For Sale O5972729 - 408 WORTHINGTON DRIVE, WINTER PARK, FL 32789 0 photos

    Bed: 5   Bath: 3.5
    Liv Area Sq Ft: 2668
       Built: 1955   Tax: $6,648 (2020)
    Community: Kenilworth Shores Sec 01
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $4,932 (change assumption)
    Mortgage ($4,378) + Taxes in 2020 ($554)

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    Taxes:$6,648

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 127 LEWFIELD CIRCLE UNIT 127, WINTER PARK, FL 32792

    $110,0007 Days on yellowkey   MLS ID: O5971364

    REDUCED by $10,000 (8.3%) on 09/14/2021

    For Sale O5971364 - 127 LEWFIELD CIRCLE UNIT 127, WINTER PARK, FL 32792 25 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $241
       Tax: $874 (2020)
    Community: Stratford A Winter Park Condo
    Pool: No

    Condo


    Estimated Monthly Payment: $917 (change assumption)
    Mortgage ($603) + Fees ($241) + Taxes in 2020 ($73)

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    Taxes:$874

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2020

    Middle School: Tuskawilla Middle


  • 615 ELLENDALE DRIVE, WINTER PARK, FL 32792

    $309,90013 Days on yellowkey   MLS ID: O5970721

    3 Days Off yellowkey (back on 9/14/2021)

    For Sale O5970721 - 615 ELLENDALE DRIVE, WINTER PARK, FL 32792 14 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1410
       Built: 1958   Tax: $2,229 (2020)
    Community: Winter Park Estates
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,884 (change assumption)
    Mortgage ($1,698) + Taxes in 2020 ($186)

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    Taxes:$2,229

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 1537 SUGARWOOD CIRCLE, WINTER PARK, FL 32792

    $498,00010 Days on yellowkey   MLS ID: O5971137

    3 Days Off yellowkey (back on 9/14/2021)

    For Sale O5971137 - 1537 SUGARWOOD CIRCLE, WINTER PARK, FL 32792 71 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3116
       Built: 1985
    Monthly Fee: $22
       Tax: $2,760 (2020)
    Community: Amberwood Unit 1
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $2,981 (change assumption)
    Mortgage ($2,729) + Fees ($22) + Taxes in 2020 ($230)

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    Taxes:$2,760

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2020

    Middle School: Tuskawilla Middle


  • 3676 HEDGEWOOD DRIVE, WINTER PARK, FL 32792

    $312,0003 Days on yellowkey   MLS ID: O5972795

    For Sale O5972795 - 3676 HEDGEWOOD DRIVE, WINTER PARK, FL 32792 35 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1310
       Built: 1964   Tax: $1,026 (2020)
    Community: Eastbrook Sub
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,795 (change assumption)
    Mortgage ($1,710) + Taxes in 2020 ($86)

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    Taxes:$1,026

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 223 E CANTON AVENUE UNIT 223, WINTER PARK, FL 32789

    $510,0003 Days on yellowkey   MLS ID: O5972840

    For Sale O5972840 - 223 E CANTON AVENUE UNIT 223, WINTER PARK, FL 32789 32 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1040
       Built: 1971   Tax: $3,989 (2020)
    Community: Village Winterset Inc
    Pool: No

    Condo


    Estimated Monthly Payment: $3,127 (change assumption)
    Mortgage ($2,794) + Taxes in 2020 ($332)

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    Taxes:$3,989

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 881 JULIAN STREET, WINTER PARK, FL 32789

    $415,0003 Days on yellowkey   MLS ID: O5972882

    For Sale O5972882 - 881 JULIAN STREET, WINTER PARK, FL 32789 62 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1300
       Built: 1954   Tax: $2,681 (2020)
    Community: Dubsdread Heights
    Pool: No

    Single Family


    Estimated Monthly Payment: $2,497 (change assumption)
    Mortgage ($2,274) + Taxes in 2020 ($223)

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    Taxes:$2,681

    Elementary School: Killarney Elem

    High School: Edgewater High

    Tax Year: 2020

    Middle School: College Park Middle


  • 1409 CHAPMAN CIRCLE, WINTER PARK, FL 32789

    $1,150,00034 Days on yellowkey   MLS ID: O5965932

    REDUCED by $45,000 (3.8%) on 09/14/2021

    For Sale O5965932 - 1409 CHAPMAN CIRCLE, WINTER PARK, FL 32789 48 photos

    Bed: 3   Bath: 3.5
    Liv Area Sq Ft: 3043
       Built: 2003
    Monthly Fee: $235
       Tax: $10,696 (2020)
    Community: Windsong Elizabeths Walk 4381
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $7,428 (change assumption)
    Mortgage ($6,301) + Fees ($235) + Taxes in 2020 ($891)

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    Taxes:$10,696

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 728 ROUGHBEARD ROAD, WINTER PARK, FL 32792

    $480,00077 Days on yellowkey   MLS ID: O5955267

    8 Days Off yellowkey (back on 9/14/2021)

    REDUCED by $19,000 (3.8%) on 09/14/2021

    For Sale O5955267 - 728 ROUGHBEARD ROAD, WINTER PARK, FL 32792 26 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1931
       Built: 1969
    Monthly Fee: $4
       Tax: $5,655 (2020)
    Community: Winter Park Pines
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $3,105 (change assumption)
    Mortgage ($2,630) + Fees ($4) + Taxes in 2020 ($471)

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    Taxes:$5,655

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 2034 EAST END AVENUE, WINTER PARK, FL 32789

    $1,049,000161 Days on yellowkey   MLS ID: O5935754

    REDUCED by $20,000 (1.9%) on 09/14/2021

    For Sale O5935754 - 2034 EAST END AVENUE, WINTER PARK, FL 32789 41 photos

    Bed: 3   Bath: 3.5
    Liv Area Sq Ft: 2714
       Built: 2019   Tax: $7,599 (2020)
    Community: Edgewood Sub
    Pool: No

    Single Family


    Estimated Monthly Payment: $6,381 (change assumption)
    Mortgage ($5,748) + Taxes in 2020 ($633)

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    Taxes:$7,599

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Audubon Park K-8


  • 1024 TUSCANY PLACE, WINTER PARK, FL 32789

    $1,225,00094 Days on yellowkey   MLS ID: O5951141

    6 Days Off yellowkey (back on 9/13/2021)

    REDUCED by $50,000 (3.9%) on 07/23/2021

    For Sale O5951141 - 1024 TUSCANY PLACE, WINTER PARK, FL 32789 73 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 3876
       Built: 1979
    Monthly Fee: $79
       Tax: $6,429 (2020)
    Community: Tuscany Place
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $7,327 (change assumption)
    Mortgage ($6,712) + Fees ($79) + Taxes in 2020 ($536)

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    Taxes:$6,429

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 1540 GLENCOE ROAD, WINTER PARK, FL 32789

    $1,750,00053 Days on yellowkey   MLS ID: O5944753

    7 Days Off yellowkey (back on 9/13/2021)

    INCREASED by $151,000 (9.4%) on 07/30/2021

    For Sale O5944753 - 1540 GLENCOE ROAD, WINTER PARK, FL 32789 72 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 4905
       Built: 1986   Tax: $11,050 (2020)
    Community: Virginia Heights
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $10,510 (change assumption)
    Mortgage ($9,589) + Taxes in 2020 ($921)

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    Taxes:$11,050

    Elementary School: Baldwin Park Elementary

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Audubon Park K-8


  • 2246 KING HENRYS COURT, WINTER PARK, FL 32792

    $449,3003 Days on yellowkey   MLS ID: O5972725

    For Sale O5972725 - 2246 KING HENRYS COURT, WINTER PARK, FL 32792 38 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2609
       Built: 1969
    Monthly Fee: $2
       Tax: $2,578 (2020)
    Community: Winter Woods
    Pool: No

    Single Family


    Estimated Monthly Payment: $2,679 (change assumption)
    Mortgage ($2,462) + Fees ($2) + Taxes in 2020 ($215)

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    Taxes:$2,578

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 1821 ANZLE AVENUE, WINTER PARK, FL 32789

    $740,00071 Days on yellowkey   MLS ID: O5954021

    REDUCED by $34,900 (4.5%) on 09/13/2021

    For Sale O5954021 - 1821 ANZLE AVENUE, WINTER PARK, FL 32789 42 photos

    Bed: 5   Bath: 3.5
    Liv Area Sq Ft: 2195
       Built: 2000   Tax: $5,140 (2020)
    Community: Sylvan Heights
    Pool: No

    Single Family


    Estimated Monthly Payment: $4,483 (change assumption)
    Mortgage ($4,055) + Taxes in 2020 ($428)

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    Taxes:$5,140

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 299 LEWFIELD CIRCLE UNIT 299, WINTER PARK, FL 32792

    $119,9004 Days on yellowkey   MLS ID: O5972663

    For Sale O5972663 - 299 LEWFIELD CIRCLE UNIT 299, WINTER PARK, FL 32792 0 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 678
       Built: 1973
    Monthly Fee: $241
       Tax: $913 (2020)
    Community: Stratford A Winter Park Condo
    Pool: No

    Condo


    Estimated Monthly Payment: $974 (change assumption)
    Mortgage ($657) + Fees ($241) + Taxes in 2020 ($76)

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    Taxes:$913

    Elementary School: English Estates Elementary

    High School: Lake Howell High

    Tax Year: 2020

    Middle School: Tuskawilla Middle


  • 2235 HOWARD DRIVE, WINTER PARK, FL 32789

    $749,00041 Days on yellowkey   MLS ID: O5963792

    REDUCED by $50,900 (6.4%) on 09/13/2021

    For Sale O5963792 - 2235 HOWARD DRIVE, WINTER PARK, FL 32789 37 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2420
       Built: 1957   Tax: $4,526 (2020)
    Community: Lake Forest Park
    Pool: No

    Single Family


    Estimated Monthly Payment: $4,481 (change assumption)
    Mortgage ($4,104) + Taxes in 2020 ($377)

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    Taxes:$4,526

    Elementary School: None

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Audubon Park K-8




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

Winter Park home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Winter Park. You can use our website to view Multiple Listing Service (MLS) data on Winter Park Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Park listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, South Broward Board of REALTORS®, MIAMI MLS, JTHS MLS, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2021 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.